# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Christer B. Aakeroy, Pierangelo Metrangolo, Giuseppe Resnati' _publ_contact_author_email ;aakeroy@ksu.edu, pierangelo.metrangolo@polimi.it, giuseppe.resnati@polimi.it ; loop_ _publ_author_name _publ_author_address C.B.Aakeroy ;Department of Chemistry Kansas State University ; J.Desper ;Department of Chemistry Kansas State University ; B.A.Helfrich ;Department of Chemistry Kansas State University ; P.Metrangolo ;NFMLab-DCMIC University of Milan ; T.Pilati ;NFMLab-DCMIC University of Milan ; ; Resnati ; ;NFMLab-DCMIC University of Milan ; Stevenazzi ;NFMLab-DCMIC University of Milan ; _publ_section_title ; Combining halogen bonds and hydrogen bonds in the modular assembly of heteromeric infinite 1-D chains ; data_1 _database_code_depnum_ccdc_archive 'CCDC 647524' _audit_creation_method SHELXL-97 _chemical_name_systematic ; isonicotinamide, I2 ; _chemical_name_common 'isonicotinamide, I2' _chemical_melting_point ? _chemical_formula_moiety ; (C6 H6 N2 O) (I2) ; _chemical_formula_sum 'C6 H6 I2 N2 O' _chemical_formula_weight 375.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6928(10) _cell_length_b 7.7411(10) _cell_length_c 8.1841(11) _cell_angle_alpha 80.734(2) _cell_angle_beta 72.131(2) _cell_angle_gamma 85.702(2) _cell_volume 457.64(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 28.05 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.728 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 6.820 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.711 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3221 _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 28.91 _reflns_number_total 2051 _reflns_number_gt 1668 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2^, conventional R-factors R are based on F, with F set to zero for negative F2^. The threshold expression of F2^ > 2sigma(F2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s2^(Fo2^)+(0.0300P)2^+0.0000P] where P=(Fo2^+2Fc2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2051 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0723 _refine_ls_wR_factor_gt 0.0677 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I -0.18879(4) 0.32518(4) 0.97567(4) 0.02539(11) Uani 1 1 d . . . N1 N -0.0091(5) 0.2258(5) 0.7041(5) 0.0255(9) Uani 1 1 d . . . I2 I -0.38898(5) 0.45005(4) 1.28211(4) 0.03194(12) Uani 1 1 d . . . C2 C 0.1377(6) 0.1235(6) 0.7001(6) 0.0279(10) Uani 1 1 d . . . H2 H 0.1678 0.0861 0.8020 0.033 Uiso 1 1 calc R . . C3 C 0.2464(6) 0.0715(6) 0.5470(6) 0.0256(10) Uani 1 1 d . . . H3 H 0.3461 -0.0046 0.5460 0.031 Uiso 1 1 calc R . . C4 C 0.2044(6) 0.1350(6) 0.3936(6) 0.0217(9) Uani 1 1 d . . . C5 C 0.0533(6) 0.2428(6) 0.4013(6) 0.0255(10) Uani 1 1 d . . . H5 H 0.0236 0.2876 0.3005 0.031 Uiso 1 1 calc R . . C6 C -0.0540(7) 0.2844(6) 0.5588(6) 0.0265(10) Uani 1 1 d . . . H6 H -0.1591 0.3540 0.5646 0.032 Uiso 1 1 calc R . . O7 O 0.4392(5) -0.0461(5) 0.2360(4) 0.0343(9) Uani 1 1 d . . . N7 N 0.3165(6) 0.1647(5) 0.0788(5) 0.0313(10) Uani 1 1 d . . . H7A H 0.3834 0.1347 -0.0181 0.038 Uiso 1 1 calc R . . H7B H 0.2393 0.2511 0.0795 0.038 Uiso 1 1 calc R . . C7 C 0.3324(7) 0.0775(6) 0.2280(6) 0.0251(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.02621(18) 0.02820(19) 0.02233(17) -0.00584(13) -0.00719(13) 0.00008(12) N1 0.023(2) 0.028(2) 0.026(2) -0.0065(17) -0.0068(16) -0.0007(16) I2 0.0318(2) 0.0402(2) 0.02304(18) -0.01015(14) -0.00573(13) 0.00528(15) C2 0.025(3) 0.033(3) 0.027(2) -0.002(2) -0.011(2) 0.001(2) C3 0.019(2) 0.033(3) 0.025(2) -0.004(2) -0.0077(18) 0.0050(19) C4 0.024(2) 0.021(2) 0.023(2) -0.0088(18) -0.0082(18) -0.0014(18) C5 0.026(2) 0.026(2) 0.024(2) -0.0036(19) -0.0086(19) 0.0035(19) C6 0.026(2) 0.030(3) 0.026(2) -0.006(2) -0.013(2) 0.005(2) O7 0.034(2) 0.041(2) 0.0243(18) -0.0084(16) -0.0044(15) 0.0143(17) N7 0.034(2) 0.037(2) 0.019(2) -0.0073(18) -0.0047(17) 0.0132(19) C7 0.030(3) 0.022(2) 0.026(2) -0.0080(19) -0.011(2) -0.0007(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 N1 2.439(4) . ? I1 I2 2.7898(5) . ? I1 I2 6.3972(8) 2_468 ? N1 C2 1.325(6) . ? N1 C6 1.340(6) . ? I2 I2 3.6314(7) 2_468 ? C2 C3 1.378(6) . ? C2 H2 0.9300 . ? C3 C4 1.396(7) . ? C3 H3 0.9300 . ? C4 C5 1.370(6) . ? C4 C7 1.522(6) . ? C5 C6 1.374(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? O7 C7 1.221(6) . ? N7 C7 1.332(6) . ? N7 H7A 0.8600 . ? N7 H7B 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 I1 I2 178.05(9) . . ? N1 I1 I2 175.10(10) . 2_468 ? C2 N1 C6 120.9(4) . . ? C2 N1 I1 119.7(3) . . ? C6 N1 I1 119.3(3) . . ? I1 I2 I2 170.00(2) . 2_468 ? N1 C2 C3 121.0(5) . . ? N1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C2 C3 C4 118.9(4) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 118.8(4) . . ? C5 C4 C7 124.6(4) . . ? C3 C4 C7 116.6(4) . . ? C4 C5 C6 119.6(5) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? N1 C6 C5 120.7(4) . . ? N1 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C7 N7 H7A 120.0 . . ? C7 N7 H7B 120.0 . . ? H7A N7 H7B 120.0 . . ? O7 C7 N7 123.3(4) . . ? O7 C7 C4 120.0(4) . . ? N7 C7 C4 116.7(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C3 -1.3(7) . . . . ? I1 N1 C2 C3 -177.1(3) . . . . ? N1 C2 C3 C4 2.9(7) . . . . ? C2 C3 C4 C5 -1.9(7) . . . . ? C2 C3 C4 C7 178.2(4) . . . . ? C3 C4 C5 C6 -0.7(7) . . . . ? C7 C4 C5 C6 179.2(4) . . . . ? C2 N1 C6 C5 -1.4(7) . . . . ? I1 N1 C6 C5 174.4(3) . . . . ? C4 C5 C6 N1 2.4(7) . . . . ? C5 C4 C7 O7 -164.3(5) . . . . ? C3 C4 C7 O7 15.6(6) . . . . ? C5 C4 C7 N7 13.7(7) . . . . ? C3 C4 C7 N7 -166.4(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7B I1 0.86 3.25 3.984(4) 145.1 2_566 N7 H7B I2 0.86 3.40 3.785(4) 110.6 2_566 C6 H6 I2 0.93 3.28 3.945(5) 129.8 1_554 N7 H7A O7 0.86 2.07 2.923(5) 173.8 2_655 _diffrn_measured_fraction_theta_max 0.849 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.060 _refine_diff_density_min -1.088 _refine_diff_density_rms 0.173 #END data_2 _database_code_depnum_ccdc_archive 'CCDC 647525' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 428 _chemical_formula_moiety '2(C6 H6 N2 O), C6 F4 I2' _chemical_formula_sum 'C18 H12 F4 I2 N4 O2' _chemical_formula_weight 646.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.247(3) _cell_length_b 5.0710(9) _cell_length_c 21.279(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.911(6) _cell_angle_gamma 90.00 _cell_volume 2090.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 6710 _cell_measurement_theta_min 2.445 _cell_measurement_theta_max 28.830 _exptl_crystal_description 'elongated table' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.053 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 3.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_absorpt_correction_T_min 0.802893 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area-detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 58508 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 31.34 _reflns_number_total 6507 _reflns_number_gt 5096 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2^, conventional R-factors R are based on F, with F set to zero for negative F2^. The threshold expression of F2^ > 2sigma(F2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The free refinement of amine groups gave unsatisfactory results because some H atoms of these groups were not well-defined. Consequently, the N-H distances of both independent molecules were restrained to the same value and the NH2 group were restrained to have similar Ueq. The SHELX-97 instructions used to restraint the refinement were: SADI N2A H1NA N2A H2NA N2B H1NB N2B H2NB SIMU N2A H1NA H2NA SIMU N2B H1NB H2NB ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s2^(Fo2^)+(0.0411P)2^+1.2183P] where P=(Fo2^+2Fc2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6507 _refine_ls_number_parameters 319 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0813 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.24162(13) 0.2828(6) 0.38402(12) 0.0488(6) Uani 1 1 d . . . C2 C 0.25428(14) 0.1427(6) 0.44163(14) 0.0542(6) Uani 1 1 d . . . C3 C 0.30841(15) 0.2030(7) 0.49545(14) 0.0581(7) Uani 1 1 d . . . C4 C 0.35335(14) 0.4047(7) 0.49447(14) 0.0559(6) Uani 1 1 d . . . C5 C 0.34151(16) 0.5431(6) 0.43657(16) 0.0578(7) Uani 1 1 d . . . C6 C 0.28678(16) 0.4854(6) 0.38268(14) 0.0542(6) Uani 1 1 d . . . I1 I 0.159947(9) 0.18294(4) 0.301633(8) 0.05638(7) Uani 1 1 d . . . I2 I 0.436405(10) 0.49066(5) 0.576643(10) 0.06923(8) Uani 1 1 d . . . F1 F 0.21321(11) -0.0601(5) 0.44606(10) 0.0777(6) Uani 1 1 d . . . F2 F 0.31734(12) 0.0543(5) 0.54932(9) 0.0863(6) Uani 1 1 d . . . F3 F 0.38281(12) 0.7427(5) 0.43166(12) 0.0849(6) Uani 1 1 d . . . F4 F 0.27763(12) 0.6289(4) 0.32827(10) 0.0760(5) Uani 1 1 d . . . N1A N 0.05026(14) 0.0255(6) 0.18964(13) 0.0644(7) Uani 1 1 d . . . C1A C -0.00652(17) 0.1693(7) 0.16943(14) 0.0606(7) Uani 1 1 d . . . H1A H -0.0129(18) 0.303(7) 0.1946(17) 0.063(10) Uiso 1 1 d . . . C2A C -0.05644(15) 0.1298(6) 0.11079(13) 0.0540(6) Uani 1 1 d . . . H2A H -0.097(2) 0.249(8) 0.0981(18) 0.072(10) Uiso 1 1 d . . . C3A C -0.04786(12) -0.0724(5) 0.07059(11) 0.0413(5) Uani 1 1 d . . . C4A C 0.01045(15) -0.2262(6) 0.09134(15) 0.0569(7) Uani 1 1 d . . . H4A H 0.0159(18) -0.377(7) 0.0657(17) 0.068(10) Uiso 1 1 d . . . C5A C 0.05816(18) -0.1671(7) 0.15065(17) 0.0695(9) Uani 1 1 d . . . H5A H 0.101(2) -0.249(8) 0.1654(19) 0.075(11) Uiso 1 1 d . . . C6A C -0.10018(13) -0.1325(4) 0.00635(12) 0.0428(5) Uani 1 1 d . . . O1A O -0.10422(11) -0.3548(3) -0.01758(10) 0.0604(5) Uani 1 1 d . . . N2A N -0.14045(14) 0.0634(5) -0.02228(12) 0.0588(6) Uani 1 1 d DU . . H1NA H -0.1299(19) 0.213(5) -0.0078(18) 0.071(10) Uiso 1 1 d DU . . H2NA H -0.1722(16) 0.039(7) -0.0560(13) 0.072(10) Uiso 1 1 d DU . . N1B N 0.55076(13) 0.6151(6) 0.68785(13) 0.0640(7) Uani 1 1 d . . . C1B C 0.57106(16) 0.4613(7) 0.74017(18) 0.0622(8) Uani 1 1 d . . . H1B H 0.540(2) 0.311(8) 0.744(2) 0.083(12) Uiso 1 1 d . . . C2B C 0.63218(16) 0.4957(5) 0.78908(15) 0.0519(6) Uani 1 1 d . . . H2B H 0.6407(16) 0.384(7) 0.8245(16) 0.052(8) Uiso 1 1 d . . . C3B C 0.67441(13) 0.7027(4) 0.78400(11) 0.0406(5) Uani 1 1 d . . . C4B C 0.65324(15) 0.8664(5) 0.73024(14) 0.0517(6) Uani 1 1 d . . . H4B H 0.6789(17) 1.010(6) 0.7260(16) 0.056(9) Uiso 1 1 d . . . C5B C 0.59161(18) 0.8144(7) 0.68326(16) 0.0635(8) Uani 1 1 d . . . H5B H 0.5757(19) 0.932(7) 0.6475(19) 0.070(10) Uiso 1 1 d . . . C6B C 0.74114(13) 0.7565(5) 0.83485(12) 0.0441(5) Uani 1 1 d . . . O1B O 0.75942(12) 0.9842(3) 0.85021(11) 0.0632(6) Uani 1 1 d . . . N2B N 0.77872(13) 0.5505(4) 0.86100(12) 0.0532(6) Uani 1 1 d DU . . H1NB H 0.7647(15) 0.404(4) 0.8479(14) 0.043(7) Uiso 1 1 d DU . . H2NB H 0.8126(13) 0.576(7) 0.8912(13) 0.052(8) Uiso 1 1 d DU . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0410(12) 0.0624(15) 0.0390(11) -0.0065(11) 0.0055(9) 0.0026(11) C2 0.0434(13) 0.0717(18) 0.0454(13) -0.0037(12) 0.0096(10) -0.0079(12) C3 0.0482(14) 0.082(2) 0.0412(13) 0.0006(13) 0.0079(11) -0.0006(14) C4 0.0427(13) 0.0722(17) 0.0471(14) -0.0113(13) 0.0044(10) -0.0007(13) C5 0.0508(15) 0.0591(16) 0.0591(16) -0.0102(13) 0.0093(12) -0.0086(12) C6 0.0551(16) 0.0595(16) 0.0442(13) -0.0029(11) 0.0085(11) 0.0002(12) I1 0.04549(10) 0.07208(14) 0.04362(10) -0.00616(8) 0.00046(7) 0.00318(8) I2 0.04737(11) 0.08888(17) 0.05930(13) -0.02054(10) -0.00358(8) 0.00030(9) F1 0.0655(11) 0.1013(14) 0.0598(11) 0.0094(10) 0.0079(9) -0.0310(11) F2 0.0799(13) 0.1229(18) 0.0447(9) 0.0175(11) 0.0004(9) -0.0167(13) F3 0.0796(14) 0.0765(13) 0.0901(15) -0.0043(11) 0.0115(12) -0.0295(11) F4 0.0913(14) 0.0685(11) 0.0594(11) 0.0141(9) 0.0079(10) -0.0075(10) N1A 0.0570(15) 0.0753(17) 0.0466(12) -0.0054(12) -0.0074(11) 0.0008(12) C1A 0.0654(18) 0.0632(18) 0.0435(14) -0.0116(13) 0.0004(12) 0.0029(14) C2A 0.0532(15) 0.0517(14) 0.0456(13) -0.0065(11) -0.0037(11) 0.0105(12) C3A 0.0408(11) 0.0373(11) 0.0395(11) 0.0001(9) 0.0020(9) -0.0044(9) C4A 0.0501(15) 0.0568(16) 0.0551(15) -0.0081(13) 0.0018(12) 0.0093(12) C5A 0.0501(16) 0.081(2) 0.0625(18) -0.0071(16) -0.0075(13) 0.0174(15) C6A 0.0453(12) 0.0337(11) 0.0418(11) -0.0014(9) 0.0008(9) -0.0052(9) O1A 0.0668(12) 0.0345(9) 0.0614(12) -0.0071(8) -0.0107(9) 0.0007(8) N2A 0.0699(16) 0.0360(11) 0.0510(13) -0.0059(9) -0.0130(11) 0.0029(10) N1B 0.0478(13) 0.0705(16) 0.0594(14) -0.0138(13) -0.0068(11) 0.0004(12) C1B 0.0496(15) 0.0579(17) 0.073(2) -0.0136(15) 0.0079(14) -0.0123(13) C2B 0.0547(15) 0.0439(13) 0.0509(14) -0.0003(11) 0.0056(12) -0.0080(11) C3B 0.0448(12) 0.0324(10) 0.0385(11) -0.0064(8) 0.0026(9) -0.0005(9) C4B 0.0522(14) 0.0429(13) 0.0509(14) 0.0058(11) 0.0008(11) -0.0025(11) C5B 0.0630(18) 0.0639(18) 0.0499(15) 0.0035(13) -0.0050(13) 0.0069(15) C6B 0.0512(13) 0.0312(10) 0.0399(11) -0.0025(9) -0.0024(10) -0.0025(9) O1B 0.0709(13) 0.0284(8) 0.0653(12) -0.0042(8) -0.0198(10) -0.0053(8) N2B 0.0564(13) 0.0298(10) 0.0556(13) -0.0037(9) -0.0115(10) -0.0018(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.375(4) . ? C1 C6 1.381(4) . ? C1 I1 2.092(2) . ? C2 F1 1.343(4) . ? C2 C3 1.370(4) . ? C3 F2 1.340(4) . ? C3 C4 1.373(5) . ? C4 C5 1.377(5) . ? C4 I2 2.089(3) . ? C5 F3 1.336(4) . ? C5 C6 1.374(4) . ? C6 F4 1.334(3) . ? N1A C5A 1.321(4) . ? N1A C1A 1.323(4) . ? C1A C2A 1.373(4) . ? C1A H1A 0.90(3) . ? C2A C3A 1.378(4) . ? C2A H2A 0.99(4) . ? C3A C4A 1.376(4) . ? C3A C6A 1.497(3) . ? C4A C5A 1.381(4) . ? C4A H4A 0.97(4) . ? C5A H5A 0.93(4) . ? C6A O1A 1.230(3) . ? C6A N2A 1.317(3) . ? N2A H1NA 0.82(2) . ? N2A H2NA 0.82(2) . ? N1B C1B 1.323(5) . ? N1B C5B 1.327(5) . ? C1B C2B 1.377(4) . ? C1B H1B 1.00(4) . ? C2B C3B 1.378(4) . ? C2B H2B 0.92(3) . ? C3B C4B 1.377(4) . ? C3B C6B 1.490(3) . ? C4B C5B 1.378(4) . ? C4B H4B 0.92(3) . ? C5B H5B 0.95(4) . ? C6B O1B 1.227(3) . ? C6B N2B 1.317(3) . ? N2B H1NB 0.81(2) . ? N2B H2NB 0.80(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 116.7(2) . . ? C2 C1 I1 121.3(2) . . ? C6 C1 I1 122.0(2) . . ? F1 C2 C3 118.3(3) . . ? F1 C2 C1 120.0(2) . . ? C3 C2 C1 121.8(3) . . ? F2 C3 C2 117.8(3) . . ? F2 C3 C4 120.5(3) . . ? C2 C3 C4 121.7(3) . . ? C3 C4 C5 116.7(3) . . ? C3 C4 I2 121.2(2) . . ? C5 C4 I2 122.1(2) . . ? F3 C5 C6 117.8(3) . . ? F3 C5 C4 120.4(3) . . ? C6 C5 C4 121.7(3) . . ? F4 C6 C5 118.9(3) . . ? F4 C6 C1 119.9(3) . . ? C5 C6 C1 121.3(3) . . ? C5A N1A C1A 117.1(3) . . ? N1A C1A C2A 123.7(3) . . ? N1A C1A H1A 119(2) . . ? C2A C1A H1A 117(2) . . ? C1A C2A C3A 118.7(3) . . ? C1A C2A H2A 119(2) . . ? C3A C2A H2A 122(2) . . ? C4A C3A C2A 118.3(2) . . ? C4A C3A C6A 119.4(2) . . ? C2A C3A C6A 122.3(2) . . ? C3A C4A C5A 118.5(3) . . ? C3A C4A H4A 120(2) . . ? C5A C4A H4A 122(2) . . ? N1A C5A C4A 123.7(3) . . ? N1A C5A H5A 113(2) . . ? C4A C5A H5A 123(2) . . ? O1A C6A N2A 122.8(2) . . ? O1A C6A C3A 120.6(2) . . ? N2A C6A C3A 116.6(2) . . ? C6A N2A H1NA 118(3) . . ? C6A N2A H2NA 121(3) . . ? H1NA N2A H2NA 121(4) . . ? C1B N1B C5B 117.6(3) . . ? N1B C1B C2B 123.5(3) . . ? N1B C1B H1B 118(2) . . ? C2B C1B H1B 118(2) . . ? C1B C2B C3B 118.6(3) . . ? C1B C2B H2B 117(2) . . ? C3B C2B H2B 124(2) . . ? C4B C3B C2B 118.3(2) . . ? C4B C3B C6B 119.4(2) . . ? C2B C3B C6B 122.3(2) . . ? C3B C4B C5B 119.0(3) . . ? C3B C4B H4B 121(2) . . ? C5B C4B H4B 120(2) . . ? N1B C5B C4B 123.0(3) . . ? N1B C5B H5B 118(2) . . ? C4B C5B H5B 119(2) . . ? O1B C6B N2B 122.8(2) . . ? O1B C6B C3B 120.3(2) . . ? N2B C6B C3B 116.9(2) . . ? C6B N2B H1NB 119(2) . . ? C6B N2B H2NB 118(2) . . ? H1NB N2B H2NB 123(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 F1 -178.8(3) . . . . ? I1 C1 C2 F1 -1.0(4) . . . . ? C6 C1 C2 C3 0.9(4) . . . . ? I1 C1 C2 C3 178.7(2) . . . . ? F1 C2 C3 F2 0.4(4) . . . . ? C1 C2 C3 F2 -179.3(3) . . . . ? F1 C2 C3 C4 178.9(3) . . . . ? C1 C2 C3 C4 -0.7(5) . . . . ? F2 C3 C4 C5 178.3(3) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? F2 C3 C4 I2 -0.7(4) . . . . ? C2 C3 C4 I2 -179.2(2) . . . . ? C3 C4 C5 F3 179.8(3) . . . . ? I2 C4 C5 F3 -1.2(4) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? I2 C4 C5 C6 180.0(2) . . . . ? F3 C5 C6 F4 0.4(4) . . . . ? C4 C5 C6 F4 179.2(3) . . . . ? F3 C5 C6 C1 -179.7(3) . . . . ? C4 C5 C6 C1 -0.9(5) . . . . ? C2 C1 C6 F4 179.8(3) . . . . ? I1 C1 C6 F4 2.0(4) . . . . ? C2 C1 C6 C5 -0.1(4) . . . . ? I1 C1 C6 C5 -177.9(2) . . . . ? C5A N1A C1A C2A -0.4(5) . . . . ? N1A C1A C2A C3A 0.7(5) . . . . ? C1A C2A C3A C4A 0.2(5) . . . . ? C1A C2A C3A C6A 179.0(3) . . . . ? C2A C3A C4A C5A -1.4(5) . . . . ? C6A C3A C4A C5A 179.8(3) . . . . ? C1A N1A C5A C4A -0.8(6) . . . . ? C3A C4A C5A N1A 1.8(6) . . . . ? C4A C3A C6A O1A 23.3(4) . . . . ? C2A C3A C6A O1A -155.4(3) . . . . ? C4A C3A C6A N2A -156.5(3) . . . . ? C2A C3A C6A N2A 24.8(4) . . . . ? C5B N1B C1B C2B -0.8(5) . . . . ? N1B C1B C2B C3B 0.7(5) . . . . ? C1B C2B C3B C4B 0.3(4) . . . . ? C1B C2B C3B C6B 179.4(3) . . . . ? C2B C3B C4B C5B -1.2(4) . . . . ? C6B C3B C4B C5B 179.7(3) . . . . ? C1B N1B C5B C4B -0.1(5) . . . . ? C3B C4B C5B N1B 1.1(5) . . . . ? C4B C3B C6B O1B 37.5(4) . . . . ? C2B C3B C6B O1B -141.6(3) . . . . ? C4B C3B C6B N2B -141.7(3) . . . . ? C2B C3B C6B N2B 39.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.100 _refine_diff_density_min -0.741 _refine_diff_density_rms 0.077 #END --CCDCCONTENTSEPARATOR--